Boron trifluoride etherate → HCID 23401463, compound

HRID 1063396Notes

Reaction equation

HRID 1063396 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[C:4]2[C:9]([CH2:12][CH:13](N)CO)=[CH:10][NH:11][C:3]=12.[C:17]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:21])[CH2:18][CH2:19][CH3:20].B(F)(F)[F:29].CCOCC>C(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C:17]1([CH2:18][CH2:19][CH3:20])[C:10]2[NH:11][C:3]3[C:4]([C:9]=2[CH2:12][CH2:13][O:21]1)=[C:5]([Br:8])[C:6]([F:29])=[CH:7][C:2]=3[CH3:1])[CH3:27]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 238498Ethyl 3-oxohexanoateHCID 90471058HCID 90471058, compound

Product 1

HCID 23401463HCID 23401463, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-7-methyl tryptophol (400 mg g, 1.47 mmol) and ethyl butyrylacetate (0.28 mL, 1.76 mmol) in CH2Cl2 (5 mL) was added BF3.OEt2 (0.22 mL, 1.76 mmol) dropwise at room temperature. The solution was stirred for 2 hours and then washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 15% EtOAc in hexanes) to give 496 mg (82%) of title compound as a pale yellow solid. Mp=137-138° C.; 1H NMR (CDCl3): 300 MHz δ 9.73 (bs, 1H), 6.76 (d, J=10.1 Hz, 1H), 4.21 (m, 2H), 4.05 (m, 1H), 3.91 (m, 1H), 3.05-2.89 (m, 4H), 2.53 (s, 3H), 2.07 (m, 1H), 1.92 (m, 1H), 1.38 (m, 1H), 1.30 (t, J=6.98 Hz, 3H), 1.21 (m, 1H), 0.89 (t, J=7.08 Hz, 3H).

Workup

  1. washwashed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (silica, 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-905d24b67f2b4ae888f895159c47a5d1
Source dataset
uspto-grants-2005_11
Patent number
US06964979B2

Reaction notes

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